Hou, Xue-Mei, Li, Yue-Ying, Shi, Yun-Wei, Fang, Yao-Wei, Chao, Rong, Gu, Yu-Cheng, Wang, Chang-Yun and Shao, Chang-Lun (2019) Integrating Molecular Networking and 1 H NMR To Target the Isolation of Chrysogeamides from a Library of Marine-Derived Penicillium Fungi . The Journal of Organic Chemistry, 84 (3). pp. 1228-1237. DOI 10.1021/acs.joc.8b02614.

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Abstract

A challenging problem in natural product discovery is to rapidly dereplicate known compounds and expose novel ones from complicated components. Herein, integrating the LC-MS/MS-dependent molecular networking and 1H NMR techniques efficiently and successfully enabled the targeted identification of seven new cyclohexadepsipeptides, chrysogeamides A–G (1–7), from the coral-derived fungus Penicillium chrysogenum (CHNSCLM-0003) which was targeted from a library of marine-derived Penicillium fungi. Compound 4 features a rare 3-hydroxy-4-methylhexanoic acid (HMHA) moiety which was first discovered from marine-derived organisms. Interestingly, isotope-labeling feeding experiments confirmed that 13C1-l-Leu was transformed into 13C1-d-Leu moiety, indicating that d-Leu could be isomerized from l-Leu. Compounds 1 and 2 obviously promoted angiogenesis in zebrafish at 1.0 μg/mL with nontoxic to embryonic zebrafish at 100 μg/mL. Combining molecular networking with 1H NMR as a discovery tool will be implemented as a systematic strategy, not only for known compounds dereplication but also for untapped reservoir discovery.

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